Tuscany – To Chianti

Tuscany, Italy

Holiday overview




Self Guided




Jan - Dec


£ 830 pp


6 nights

This route is a complement to our long-established ‘South to Siena’ walk. Walking holidays Tuscany offers you spectacular self guided walking through the countryside to the north of Siena.

This route is a complement to our long-established ‘South to Siena’ walk. Including the wonderful towns of San Gimignano (with its Vernaccia vineyards) and the Etruscan town of Volterra, it travels through the countryside to the north of Siena, with the first night in the great medieval town of Siena itself, home of the Palio horserace. Hilltop fortified towns, Etruscan ruins, medieval boroughs, vines, and olive groves are the highlights of the journey. A self-guided walking holiday, this is a route for anyone of moderate fitness.



£830.00 per person. Single supplement £165.00.



  • 6 nights in 3/4 star hotels or on occasion similar standard agriturismo with double room and private bath
  • 6 breakfasts
  • Route notes and itineraries
  • Luggage transfers
  • Transfers as per programme
  • Local emergency back up.


Not Included:

  • Transport from/to home
  • Meals not mentioned in the programme
  • Drinks with meals
  • Insurance
  • Anything not specifically mentioned in programme.


Departure Dates:

April to end of October – start on the day of your choice.

Day 1:

Welcome to Siena, the best preserved medieval city in Europe. If you have time, walk the easy 3 km exploratory route through the town. Overnight Siena.


Day 2:

Siena – Strove.

Transfer to S. Colomba and walk through the beautiful woods of the Montagno La Sensese. Walk along rolling hills, on paths, tracks and gravel roads.  Overnight Strove (for 2 nights).

12 kms/8 miles.


Day 3:

Strove – Monteriggione – Strove.

An easy to moderate walk to the small medieval hilltop village of Monteriggione with its perfectly preserved walls and watchtowers. Return to Strove for overnight.

14 kms/8.75 miles


Day 4:

Strove – Colle di Val d’Elsa.

Pleasant walk in classic Tuscan countryside to the medieval market town of Colle di Val d’Elsa, famous for its crystal production since the Middle Ages, and with an interesting Etruscan museum. Overnight Colle.

10 kms/6.25 miles.


Day 5:

Colle di Val d’Elsa – San Gimignano.

An easy to moderate walk with tremendous views of Tuscan towns and countryside. Today you are following the Via Francigena, the medieval Pilgrim way to Rome, which threaded across Europe from Canterbury, rivalling the ‘Camino di Santiago’. Overnight in San Gimignano, the city of medieval towers.

14 kms/8.75 miles.


Day 6:

San Gimignano – Sensano – Volterra.

Enjoy fabulous countryside views, including the celebrated Vernaccia vineyards, passing near the ruins of a medieval castle and through a cool evergreen oak wood. Transfer from Sensano to the Etruscan town of Volterra for overnight.

14kms/8.75 miles.


Day 7:

Departure after breakfast.


Additional options:

We can also arrange for extra nights along the route – please ask for prices.